Crooked Road Music Trail Eastern Loop – Songs of The Shenandoah & Bluegrass from The Blue Ridge

The Crooked Road winds through almost 300 miles of scenic terrain in southwest Virginia, including 19 counties and 54 towns. Enjoy tours & tastings with lots of music inbetween. To list all of the legends along the Crooked Road, you would need an encyclopedia of volumes from A-Z!

Bring your Dancing Shoes!

6 Days /5 Nights

Group size

Tour Includes: 5 nights’ accommodation; 5 breakfasts; 5 lunches; 5 dinners; admissions, entrance, and guide fees as stated in the itinerary, including taxes, and gratuity. Except gratuity for guide fees is not included on adult tours unless otherwise requested.
  • Distillery Taste Tour
  • Hatfield and McCoy Tour
  • Big Sandy Heritage-History Center Museum
  • Ralph Stanley Museum
  • Big Stone Gap
  • June Tolliver House
  • Historic Lays Hardware Center for the Arts
  • Natural Tunnel State Park
  • Birthplace of Country Music Museum

Sample Itinerary:
Day 1 - Distillery Tasting & Tour and Live Local Bluegrass
  • Enjoy a Taste and Tour at a local distillery.
  • Explore the rich history and culture of the Kentucky area through the lens of brewing and distilling.
  • Check-in to your local hotel and this evening, enjoy dinner and live Bluegrass/Country music. (Meals: D)
Day 2 - Loretta Lynn Birthplace, Hatfield & McCoy Tour, and Ralph Stanley Museum
  • Enjoy breakfast at the hotel prior to checking out.
  • Depart with GUIDE and visit the birthplace of Loretta Lynn, Butcher Holler. Nestled between two fog-shrouded mountains up a "holler" just two miles southeast of the coal mining camp of Van Lear, the region that inspired country music star Loretta Lynn to write some of her most famous songs, most notably “Coal Miner’s Daughter.”
  • Depart with a Coal Miner’s Lunch. Continue on to your Hatfield and McCoy Tour.  Pike County is home to most of the significant Hatfield and McCoy feud sites.
  • Visit Big Sandy Heritage-History Center Museum, which portrays the history and culture of Eastern Kentucky.  It has the largest collection of Hatfield and McCoy Feud and Big Sandy Valley Civil War artifacts.
  • Visit the Ralph Stanley Museum, a monument to Dr. Ralph Edmond Stanley, an American bluegrass artist, known for his distinctive singing and banjo playing.
  • Check-in to your hotel for the evening featuring historic gems, local artisans in all mediums, and abundant outdoor recreation. Enjoy dinner included. (Meals: B, L, D)
Day 3 - Big Stone Gap, June Toliver House, & Live Local Bluegrass
  • Enjoy breakfast at the hotel prior to departing for Big Stone Gap.
  • Meet your GUIDE and tour the Harry Meador Coal Museum. Coal is to Big Stone Gap and the entire Appalachian region what automobiles are to Detroit, corn is to Kansas and oil is to Texas. Learn about the filming of the movie, “Big Stone Gap” featuring Ashley Judd, Patrick Wilson, and Whoopi Goldberg as you drive by the home of the book’s author and director of the film, Adriana Trigiani.
  • Visit the National Historic Landmark, the Southwest Virginia Museum, a 1890s Victorian stone mansion with original oak interior. The museum's collection includes more than 25,000 pieces and state of the art exhibits telling the story of the exploration and development of Southwest Virginia from the pioneer era of the 1700s to the mining "boom and bust" era of the late 1800s.
  • Enjoy lunch included at the John Fox Jr. Museum. The museum was the home of John Fox, Jr., a famous mountain author of many novels and short stories. Most well-known are "Trail of the Lonesome Pine" and "The Little Shepherd of Kingdom Come".
  • Visit the June Tolliver House and gift shop. The first floor of the house displays antiques dating back from the turn of the century. Throughout its rooms are paintings donated by local artists, the majority of which are actors/actresses who, over the past 45 years, have held a starring role in the Trail of the Lonesome Pine Outdoor Drama.
  • Depart for your hotel, rest, and refresh before dinner included.
  • This evening, visit the Historic Lays Hardware Center for the Arts for Live Local Bluegrass! The Crooked Road comes to Coeburn every Friday night at the Historic Lays Building in downtown. Local groups entertain and provide music to "shake a leg" to on the dance floor, as well as Flat Foot Dancing. (Meals: B, L, D)
Day 4 - Natural Tunnel State Park & Birthplace of Country Music Museum
  • Enjoy breakfast at the hotel prior to checking out.
  • Travel the Daniel Boone Trail to the Natural Tunnel State Park. One of the nation's most historic routes, the Daniel Boone Wilderness Trail was blazed by the legendary frontiersman in 1775 from Long Island of the Holston at what is now Kingsport, TN, through the Cumberland Gap of Virginia and into Kentucky.
  • Stop at the Wilderness Road Blockhouse, an important landmark for frontier travelers and served as the gathering place for hundreds of pioneers traveling the Wilderness Road to Kentucky between 1775 and 1800.
  • Enjoy lunch included at a local restaurant!
  • Arrive for a tour at the Birthplace of Country Music Museum, an affiliate of the Smithsonian Institution, tells the story of the 1927 Bristol Sessions recordings by the Carter Family, Jimmie Rodgers, Ernest V. Stoneman, and others. The museum explores how this rich musical heritage lives on in today's music, and how music from this region continues to influence music around the world.
  • Check-in to your hotel for the evening and enjoy dinner included. (Meals: B, L, D)
Day 5 - Abingdon Tour, White’s Mill, and Heartwood
  • Enjoy breakfast at the hotel. Depart for Abingdon. Nestled in the mountains of Southwest Virginia, in an area of unparalleled natural beauty that is rich in tradition. You can stroll shaded, brick sidewalks and savor the ambiance of the oldest town west of the Blue Ridge Mountains; or explore a 20-block Historic District filled with outstanding examples of Federal and Victorian architecture.
  • Meet your GUIDE and tour White’s Mill, a historic grist mill dating to the mid-1800s. You will be greeted by a banjo player and storyteller. While enjoying local music you will receive a moon pie, RC cola, and local peanuts.
  • Tour the Abingdon Olive Oil Company, a tasting gallery and shop featuring over 68 varieties of Olive Oils & Balsamic Vinegars.
  • Enjoy lunch included today.
  • Meet your GUIDE at Heartwood (The Southwest Virginia Cultural Center) and enjoy a tour of Abingdon. Heartwood is tucked into Virginia’s ancient mountains and home to music, crafts, and food of the Crooked Road. Shop crafts by local artisans, juried to be the best of the best, and the most complete collection of Crooked Road old time, bluegrass, and gospel music.  Get a personal welcome to Southwest Virginia's heritage, craft, music, outdoor recreation, and scenic beauty.
  • Enjoy dinner included where chicken wings and many spicy sauces star on the American menu at this casual, automotive-themed restaurant.
  • Arrive at the remote community of Hiltons, VA for a special show at the Carter Family Fold, a rustic and eclectic theater with festival seating. Visit the restored cabin, built in the mid-1800s, where A.P. Carter was born, along with his seven brothers and sisters.  It was originally located in Little Valley, which runs parallel to Poor Valley, and had no public access. Enjoy the show prior to returning to hotel. (Meals: B, L, D)
Day 6 - Patsy Cline Hometown & Depart
  • Enjoy breakfast at the hotel prior to checking out. Arrive in historic Winchester, VA and enjoy lunch included at the George Washington Wyndham Hotel. The pristine beauty of the Shenandoah Valley has truly met its match. With marble floors, soaring ceiling heights, and the original front desk, this deco stunner still has all the appeal and ambiance of a wonderful bygone era. Completed in 1924, the George Washington offers old-world charm.
  • A Patsy Cline tribute singer will entertain you during lunch. Visit Patsy Cline’s Historic House, take a tour of Patsy Cline’s hometown where she began her radio career at Winchester Radio Station WINC in 1946 at age 14. Patsy resided here from 1948-53, longer than at any other house associated with her in the Winchester and Nashville areas, and she returned to it intermittently until her singing career began in 1957. Continue home. (Meals: B, L)


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